Probing the formation of monoalkyl carbonates and pyrocarbonates in water with electrospray ionization mass spectrometry

Vidal, Denis Tadeu Rajh; Santana, Michele Alves; Hotta, Guilherme Minoru; Godoi, Marla Narciso; Eberlin, Marcos N.; Lago, Claudimir Lúcio do

doi:10.1039/c3ra42518e

Cited by 6 publications

(5 citation statements)

References 16 publications

(31 reference statements)

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“…This nding is in agreement with our previous experiments with direct injection of MAC solutions in ESI-MS. 9 We have observed an increasing trend in production of gas-phase MAC ions as the carbonic chain increases. However, when direct injection is used, a clear understanding about this behaviour is precluded because of the possible contribution of both the alcohol and its MAC to the efficiency of ionization.…”

Section: Quantitation Of Hecasmentioning

confidence: 83%

“…However, it precludes the detection of monomethyl carbonate, because it may be previously available in the reagent or may be formed by absorption of CO 2 from the air. 9 The fragmentation of a MAC at low collisional energy yields the corresponding alkoxide by loss of CO 2 . 9 This reaction occurs even when the energy at the collisional chamber (the hexapole between the two separation quadrupoles) is set to 0 eV.…”

Section: The Development Of the Bge And Experimental Conditionsmentioning

confidence: 99%

“…Because of the complexity of the matrix and the anticipated low concentration of the HECAs, electrospray ionization/mass spectrometry (ESI-MS) was then introduced as an alternative technique. 9 The CO 2 loss at low collisional energy was the most common behaviour of the MACs in the gas phase. Although ESI-MS alone did not allow the same good quantitation approach developed for CE-C 4 D, sensitivity and selectivity were improved, which stimulated the development of the herein introduced CE-MS/ MS method.…”

Section: Introductionmentioning

confidence: 99%

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A capillary electrophoresis/tandem mass spectrometry approach for the determination of monoalkyl carbonates

et al. 2014

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Section: Quantitation Of Hecasmentioning

confidence: 83%

Section: The Development Of the Bge And Experimental Conditionsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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A capillary electrophoresis/tandem mass spectrometry approach for the determination of monoalkyl carbonates

et al. 2014

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“…In biochemistry, [2] and in food chemistry, that is, carbonated alcoholic beverages, [3] the focus is on detection and reaction of very low concentrations of carbonic ester derivatives in aqueous solution. [5] MACs or HECAs are studied from small alkyl esters to quite complex esters, for example, with sugars. [4] The biological relevance emphasizes the need for simple synthesis and characterization of HECAs as a pure substance.…”

Section: Introductionmentioning

confidence: 99%

“…The molecule investigated in this work is the methyl hemiester of carbonic acid, which we will refer to as CAME (carbonic acid monomethyl ester) in the following. In biochemistry, and in food chemistry, that is, carbonated alcoholic beverages, the focus is on detection and reaction of very low concentrations of carbonic ester derivatives in aqueous solution . MACs or HECAs are studied from small alkyl esters to quite complex esters, for example, with sugars …”

Section: Introductionmentioning

confidence: 99%

Alpha‐Carbonic Acid Revisited: Carbonic Acid Monomethyl Ester as a Solid and its Conformational Isomerism in the Gas Phase

Köck

Bernard

Podewitz

et al. 2019

Chemistry A European J

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In this work, earlier studies reporting α‐H2CO3 are revised. The cryo‐technique pioneered by Hage, Hallbrucker, and Mayer (HHM) is adapted to supposedly prepare carbonic acid from KHCO3. In methanolic solution, methylation of the salt is found, which upon acidification transforms to the monomethyl ester of carbonic acid (CAME, HO‐CO‐OCH3). Infrared spectroscopy data both of the solid at 210 K and of the evaporated molecules trapped and isolated in argon matrix at 10 K are presented. The interpretation of the observed bands on the basis of carbonic acid [as suggested originally by HHM in their publications from 1993–1997 and taken over by Winkel et al., J. Am. Chem. Soc. 2007 and Bernard et al., Angew. Chem. Int. Ed. 2011] is inferior compared with the interpretation on the basis of CAME. The assignment relies on isotope substitution experiments, including deuteration of the OH‐ and CH3‐ groups as well as 12C and 13C isotope exchange and on variation of the solvents in both preparation steps. The interpretation of the single molecule spectroscopy experiments is aided by a comprehensive calculation of high‐level ab initio frequencies for gas‐phase molecules and clusters in the harmonic approximation. This analysis provides evidence for the existence of not only single CAME molecules but also CAME dimers and water complexes in the argon matrix. Furthermore, different conformational CAME isomers are identified, where conformational isomerism is triggered in experiments through UV irradiation. In contrast to earlier studies, this analysis allows explanation of almost every single band of the complex spectra in the range between 4000 and 600 cm−1.

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Formation of isomers of anionic hemiesters of sugars and carbonic acid in aqueous medium

Santos

Vidal

Francisco

et al. 2016

Carbohydrate Research

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Probing the formation of monoalkyl carbonates and pyrocarbonates in water with electrospray ionization mass spectrometry

Cited by 6 publications

References 16 publications

A capillary electrophoresis/tandem mass spectrometry approach for the determination of monoalkyl carbonates

A capillary electrophoresis/tandem mass spectrometry approach for the determination of monoalkyl carbonates

Alpha‐Carbonic Acid Revisited: Carbonic Acid Monomethyl Ester as a Solid and its Conformational Isomerism in the Gas Phase

Formation of isomers of anionic hemiesters of sugars and carbonic acid in aqueous medium

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